JPH0356468B2 - - Google Patents
Info
- Publication number
- JPH0356468B2 JPH0356468B2 JP57107180A JP10718082A JPH0356468B2 JP H0356468 B2 JPH0356468 B2 JP H0356468B2 JP 57107180 A JP57107180 A JP 57107180A JP 10718082 A JP10718082 A JP 10718082A JP H0356468 B2 JPH0356468 B2 JP H0356468B2
- Authority
- JP
- Japan
- Prior art keywords
- polyimide
- group
- heat treatment
- developer
- photosensitive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920001721 polyimide Polymers 0.000 claims description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 239000004642 Polyimide Substances 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 27
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 description 27
- 239000010408 film Substances 0.000 description 17
- 239000002243 precursor Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- -1 vinyl compound Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004031 devitrification Methods 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical class [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- 125000006840 diphenylmethane group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/325—Non-aqueous compositions
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57107180A JPS58223149A (ja) | 1982-06-22 | 1982-06-22 | 感光性ポリイミド用現像液 |
| US06/505,206 US4547455A (en) | 1982-06-22 | 1983-06-17 | Process of forming polyimide pattern and developer therefor |
| DE8383303600T DE3370883D1 (en) | 1982-06-22 | 1983-06-22 | Developer for use in forming a polyimide pattern |
| EP83303600A EP0101165B1 (en) | 1982-06-22 | 1983-06-22 | Developer for use in forming a polyimide pattern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57107180A JPS58223149A (ja) | 1982-06-22 | 1982-06-22 | 感光性ポリイミド用現像液 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58223149A JPS58223149A (ja) | 1983-12-24 |
| JPH0356468B2 true JPH0356468B2 (en, 2012) | 1991-08-28 |
Family
ID=14452492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57107180A Granted JPS58223149A (ja) | 1982-06-22 | 1982-06-22 | 感光性ポリイミド用現像液 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4547455A (en, 2012) |
| EP (1) | EP0101165B1 (en, 2012) |
| JP (1) | JPS58223149A (en, 2012) |
| DE (1) | DE3370883D1 (en, 2012) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6042425A (ja) * | 1983-08-17 | 1985-03-06 | Toray Ind Inc | 化学線感応性重合体組成物 |
| US4656116A (en) * | 1983-10-12 | 1987-04-07 | Ciba-Geigy Corporation | Radiation-sensitive coating composition |
| US4857435A (en) * | 1983-11-01 | 1989-08-15 | Hoechst Celanese Corporation | Positive photoresist thermally stable compositions and elements having deep UV response with maleimide copolymer |
| US5059513A (en) * | 1983-11-01 | 1991-10-22 | Hoechst Celanese Corporation | Photochemical image process of positive photoresist element with maleimide copolymer |
| JPS60113993A (ja) * | 1983-11-25 | 1985-06-20 | 三菱電機株式会社 | 多層回路基板の製造方法 |
| JPS60115222A (ja) * | 1983-11-28 | 1985-06-21 | Tokyo Ohka Kogyo Co Ltd | 微細パタ−ン形成方法 |
| JPS60114575A (ja) * | 1983-11-28 | 1985-06-21 | Tokyo Ohka Kogyo Co Ltd | 乾式パタ−ン形成方法 |
| US4631249A (en) * | 1984-01-16 | 1986-12-23 | Rohm & Haas Company | Process for forming thermally stable negative images on surfaces utilizing polyglutarimide polymer in photoresist composition |
| DE3411714A1 (de) * | 1984-03-29 | 1985-10-10 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur herstellung von polyimidazol- und polyimidazopyrrolon-reliefstrukturen |
| EP0188205B1 (de) * | 1985-01-15 | 1988-06-22 | Ciba-Geigy Ag | Polyamidester-Fotoresist-Formulierungen gesteigerter Empfindlichkeit |
| US5314788A (en) * | 1986-01-24 | 1994-05-24 | Canon Kabushiki Kaisha | Matrix printed board and process of forming the same |
| US4720445A (en) * | 1986-02-18 | 1988-01-19 | Allied Corporation | Copolymers from maleimide and aliphatic vinyl ethers and esters used in positive photoresist |
| JP2511651B2 (ja) * | 1986-05-19 | 1996-07-03 | 旭化成工業株式会社 | パタ−ンを形成する方法 |
| JP2626696B2 (ja) * | 1988-04-11 | 1997-07-02 | チッソ株式会社 | 感光性重合体 |
| US4883744A (en) * | 1988-05-17 | 1989-11-28 | International Business Machines Corporation | Forming a polymide pattern on a substrate |
| US4908096A (en) * | 1988-06-24 | 1990-03-13 | Allied-Signal Inc. | Photodefinable interlevel dielectrics |
| US5354645A (en) * | 1988-08-23 | 1994-10-11 | E. I. Du Pont De Nemours And Company | Process for the production of flexographic printing reliefs |
| JP2566326B2 (ja) * | 1988-08-23 | 1996-12-25 | イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー | フレクソグラフ用印刷レリーフの作成方法 |
| DE3841854A1 (de) * | 1988-12-13 | 1990-06-21 | Hoechst Ag | Verfahren zur herstellung einer ozonresistenten flexodruckform |
| DE69030484T2 (de) * | 1989-11-30 | 1997-08-28 | Sumitomo Bakelite Co | Fotoempfindliche Harzzusammensetzung |
| JPH0415226A (ja) * | 1990-05-10 | 1992-01-20 | Chisso Corp | ヒドロキシフェニル基を有する感光性耐熱重合体 |
| JP2503103B2 (ja) * | 1990-09-25 | 1996-06-05 | 東レ株式会社 | 感光性ポリイミド用現像液 |
| US5268260A (en) * | 1991-10-22 | 1993-12-07 | International Business Machines Corporation | Photoresist develop and strip solvent compositions and method for their use |
| EP0612812B1 (en) | 1993-02-24 | 2001-07-11 | Ibiden Co, Ltd. | Resin composites and method for producing the same |
| JP3366859B2 (ja) * | 1998-03-05 | 2003-01-14 | 日立化成デュポンマイクロシステムズ株式会社 | 感光性ポリイミド前駆体用現像液及びこれを用いたパターン製造法 |
| US6372389B1 (en) * | 1999-11-19 | 2002-04-16 | Oki Electric Industry Co, Ltd. | Method and apparatus for forming resist pattern |
| US6896997B2 (en) * | 1999-11-19 | 2005-05-24 | Oki Electric Industry Co., Ltd. | Method for forming resist pattern |
| US6294259B1 (en) | 2000-07-06 | 2001-09-25 | 3M Innovative Properties Company | Polyimide hybrid adhesives |
| CN102785498A (zh) * | 2005-04-06 | 2012-11-21 | 津克成像有限责任公司 | 多色热成像方法和热印刷机 |
| TW201026513A (en) * | 2009-01-08 | 2010-07-16 | Univ Nat Cheng Kung | Imprinting process of polyimide |
| JP6087655B2 (ja) * | 2013-02-18 | 2017-03-01 | 東京応化工業株式会社 | 現像液、及び感光性樹脂組成物の現像処理方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL177718C (nl) * | 1973-02-22 | 1985-11-01 | Siemens Ag | Werkwijze ter vervaardiging van reliefstructuren uit warmte-bestendige polymeren. |
| US4093465A (en) * | 1973-08-14 | 1978-06-06 | Polychrome Corporation | Photosensitive diazo condensate compositions |
| DE2437348B2 (de) * | 1974-08-02 | 1976-10-07 | Ausscheidung in: 24 62 105 | Verfahren zur herstellung von reliefstrukturen |
| US4093461A (en) * | 1975-07-18 | 1978-06-06 | Gaf Corporation | Positive working thermally stable photoresist composition, article and method of using |
| US4180404A (en) * | 1977-11-17 | 1979-12-25 | Asahi Kasei Kogyo Kabushiki Kaisha | Heat resistant photoresist composition and process for preparing the same |
| JPS5952822B2 (ja) * | 1978-04-14 | 1984-12-21 | 東レ株式会社 | 耐熱性感光材料 |
| DE2967162D1 (en) * | 1978-09-29 | 1984-09-13 | Hitachi Ltd | Light-sensitive polymer composition |
| DE2933805A1 (de) * | 1979-08-21 | 1981-03-12 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur herstellung hochwaermebestaendiger reliefstrukturen und deren verwendung |
| US4329419A (en) * | 1980-09-03 | 1982-05-11 | E. I. Du Pont De Nemours And Company | Polymeric heat resistant photopolymerizable composition for semiconductors and capacitors |
| GB2092164B (en) * | 1980-12-17 | 1984-12-05 | Hitachi Ltd | Loght or radiation-sensitive polymer composition |
| US4403029A (en) * | 1982-09-02 | 1983-09-06 | J. T. Baker Chemical Company | Stripping compositions and methods of stripping resists |
-
1982
- 1982-06-22 JP JP57107180A patent/JPS58223149A/ja active Granted
-
1983
- 1983-06-17 US US06/505,206 patent/US4547455A/en not_active Expired - Fee Related
- 1983-06-22 DE DE8383303600T patent/DE3370883D1/de not_active Expired
- 1983-06-22 EP EP83303600A patent/EP0101165B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3370883D1 (en) | 1987-05-14 |
| EP0101165A3 (en) | 1984-10-31 |
| US4547455A (en) | 1985-10-15 |
| EP0101165B1 (en) | 1987-04-08 |
| EP0101165A2 (en) | 1984-02-22 |
| JPS58223149A (ja) | 1983-12-24 |
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